Multi-step reaction with 8 steps
1: 80 percent / Br2, CH3COOH / 5 h / Ambient temperature
2: 98 percent / p-toluenosulfonic acid / benzene / 2 h / Heating
3: 1.) tetramethylene diamine, n-butyllithium, (n-Bu)3P*CuI / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, from -78 deg C to RT, 0.5 h
4: 95 percent / 10percent aq. HCl / diethyl ether / 2 h / Ambient temperature
5: 67 percent / SO2 / thiophene / 8 h / Irradiation
6: p-toluenosulfonic acid / CH2Cl2 / 1 h / Heating
7: 82 percent / ZnO / benzene / 15 h / Heating
8: 99 percent / p-toluenosulfonic acid / toluene / 16 h / Heating
With
hydrogenchloride; n-butyllithium; CuI*P(n-Bu)3; N,N,N,N,-tetramethylethylenediamine; sulfur dioxide; bromine; toluene-4-sulfonic acid; acetic acid; zinc(II) oxide;
In
thiophene; diethyl ether; dichloromethane; toluene; benzene;
DOI:10.1021/jo00368a018